It's Complicated
by LeightonFanatic
Summary: Chuck Bass waits at a resturaunt for his Date Serena Vander Woodsen but instead serena sends her best friend blair waldorf to tell him she cant make it, Chuck's heart cant stop beating when he see's Blair and know's he have to have her. this is a chair story!


"**Now do you see why I don't go on dates Nathanial?" Chuck Bass asked his best friend on the other side of the phone. Chuck was waiting impatiently for his Date Serena Vander Woodsen at a restaurant. "**

**Relax man we both know at the end you were just going to bang her and never see her again" Nate explained **

"**That may be partly true but couldn't we just skip to the bedroom" Chuck said grinning **

"**Come on man just try I know going on dates isn't part of the "chuck Bass" life style but give it a shot you never know you might just actually like her I mean she's hot man" Nate said**

"**Blonds' aren't really my type" chuck explained **

"**Didn't seem that way when that stripper left your room earlier" Nate said chuckling **

"**Yeah well anyway it's too late I've waited too long for her already" Chuck said getting up **

"**Just give it another 10 minutes ill phone her now" Nate said **

"**Okay but if she doesn't show up in the next 10 I'm leaving" Chuck said taking his seat again and hanging up on Nate **

**XOXO**

"**Blair! Blair!" Serena Vander Woodsen said to her best friend Blair Waldorf who was just about to go out to get some flowers for her sick mom who was struggling with cancer. **

"**S I'm here what's the matter? " Blair explained **

"**I have a date with this guy and I can't make it my mom wants me over she said it's really important since you're going out could you stop at the Restaurant and tell him I'm sorry I couldn't make it please?" Serena said to Blair while leaning her shoulder's on her**

"**S that's stupid just phone him or explain things to him tomorrow" Blair said**

"**No I don't want to face him the Restaurant is near to the florist so…just stop there and tell him I'm sorry I couldn't make it" Serena said jumping into a cab about to go to her mom "I would to do it but my mom wants me on the other side of town" she repeated. **

"**Okay Okay fine I'll do it and who is he? How will I know who to look for?" Blair sighs and gets into her town car**

"**His name is Chuck Bass just ask the waiter for him" Serena said as drove away before her best friend could say bye **

"**What Chuck Bass did Serena honestly think I didn't know who he is?" Blair whispered to herself **

**The Bad boy Bachelor of the Upper East Side also known as the boy millionaire son of Bart Bass who owns Bass industries Blair knew course Bart and her father did some business last thanks giving. Blair was very interested in the Bass family so she did some research on them and came across Chuck Bass who she also know from Gossip girl she knew his reputation.**

**XOXO **

**10 Minutes Later Blair arrived at the Restaurant about to get out of the car she realised she still had the flowers in her hand she dropped it into the car and walked into the Restaurant scanning the place for chuck bass who she finally spotted.**

"**Chuck Bass is it?" Blair said tapping Chuck on the shoulder as soon as Chuck turned around his jaw dropped his face boiling heart pounding he never saw a more beautiful creature in his entire life her brown eyes was boring into his, He body checked her and thought to himself "Fucking hell this girl is gorgeous" Her cream Michael Kors dress fitted her perfectly and showed off her perfect figure it was short enough for chuck bass but not too short to make her look like a slut, her flawless skin and perfect pout made his heart skip a beat and left him speechless no one leaves "Chuck Bass speechless" **

**Finally Chuck cleared his head and was able to let words come out of his mouth "yes and to what to I owe the pleasure?" Chuck said trying to sound as flattering as ever **

**Blair rolled her eyes "My best friend Serena Vander Woodsen wanted you to know she couldn't make it" Blair explained **

**And at that moment Chuck never felt happier in his entire life and didn't regret coming on this date or he would have never seen "Her" although he was dying to find out her name. Chuck couldn't find the right way to reply to her he never felt more attracted to women in his entire life. **

"**Well that was a waste of Champagne" Chuck said chuckling **

"**Yes well Serena had an emergency" Blair replied still standing their **

"**Must have been a hell of an Emergency to stand Chuck Bass up" Chuck said standing up and fixing his tie again starring into her eyes he felt like he couldn't move away "And you are?" he said**

"**Not interested" she replied as she walked for the door chuck following at her he couldn't help but admire her ass as she walked out the door "God could this girl get more perfect" he thought **

"**Crap! Were the hell is my town car!" Blair shouted as she looked around **

"**Something wrong princess?"**

"**What does it look like my Damn town car is gone!" **

"**Relax I can give you a ride home my Limo is just there"**

"**What's the catch" Blair said as she walked closer to him, he could hear her breathing heavily, she smelt of Lilac and Lavender **

"**No catch" He said calmly guiding her to his Limo **

"**Fine, Blair agrees but only because my town car is gone"**

**Blair sat in the corner of Chuck's Limo looking through the window the entire way home. She knew Chuck was starring at her, as his hungry eye's scan Blair's figure from head to toe. **

"**See something you like?" Blair smirked**

"**Finally going to tell me your name?"**

"**In time Bass" **

**Chuck leaned forward to her pressing his lips against her ear "If you wanted to play games all you had to do is ask" he whispered to her**

**Blair leaned back to him making herself look irresistible "It must really stink knowing you lost" **

"**Oh honey I'm just getting started" Chuck lifted his hand up her thighs **

**Blair had to admit the feeling of his hands of her thighs gave her pleasure that she was ashamed of, his hands moved closer and high up her thighs she didn't know why but somehow felt like there was a connection between them spark's which she thought she would only feel when she dated "Carter Baizen" who was her ex. As Chuck drew his hands upper Blair started to get shivers up her spin. **

"**Uh ah uh don't forget I know your reputation Bass" **

**His stomach started to get butter flies as his eye's was melting into deep brown eyes. What the hell was wrong with him know one gives Chuck Bass butterflies.**

"**Is that so I wasn't aware you knew of Gossip Girl or did you just research me?"**

**Blair knew to keep quite cause she was all over Gossip Girl and she didn't want him to find out her name, she sat there just starring into his eyes not finding the right words to say her hand was still holding his from when she wanted to move it away, She quickly moved her hand from his. Not knowing that the limo already pulled over at Blair's penthouse.**

**Blair cleared her throat, "Looks like I should be leaving now" She said **

**His stomach fluttered as he continued to eye her **

"**Let me" Chuck said getting out of the car to open the door for her.**

"**Tanks for lift home" She said as she walked into her building.**

**He needed to find out who this girl is and of course he can his chuck bass he can call his PI, or Private investigator whatever the cost he wasn't going to rest until he found out her name or even see her again, he knew there was more to this girl than meets the eye.**

**XOXO**

"**Thank you so much B I couldn't thank you enough for last night! I know it must have been torture even just going near that Chuck Bass I didn't even want to go on a date with him Nate made me" Serena said as her and Blair was walking down the streets of Manhattan looking for the new fall lines they've been invited to the Marc Jacob's fashion show next week and were looking for a outfit together.**

**Although Blair had to admit she and Chuck had some type a connection last night that didn't make her regret going there and taking a life from him.**

"**No need to thank me Elizabeth Taylor I'm just glad you let Humphrey go before he left you high and dry" Blair laughed **

"**Blair! Leave Dan out of this! "**

"**I can't I just can't stop gloating that I was right!... Okay 5% of me is sorry for you"**

"**Well anyway… My mom is hosting dinner tonight for some business deal and she's making me attend be my date? "Serena said handing her hand to Blair **

"**Of course I can never past a Vander Woodsen dinner party"**

"**Great! It starts at 7"**

**XOXO**

"**Oh Bart and Charles so good to have you guys join us" Lily Vander Woodsen said as she shacked both the bass's hands **

"**Lily the pleasure is all mine it's good to see you again" Bart replied **

"**Oh Stop! And Charles my have you grown good to see you!" she said as she guided them to the dinner table that was neatly set with candles, tall champagne glasses, neatly packed plates the vegetables has arrived followed the roast as the caterers started packing it on the highly decorated table.**

"**My, my It's been a while we're is that lovely Daughter of yours Serena and your son Eric" Bart explained as he sat down**

'**Aah well Serena should be joining us shortly she's just went to pick up her friend Blair Waldorf who will be joining us" **

"**Blair Waldorf is Eleanor Waldorf's daughter is it not?" **

"**Yes that is corrected…..oh here's Eric"**

"**Eric" Bart shouted as Eric came and took a seat next to Bart Chuck was eyeing Eric from across the table Chuck liked to sit at the end it was near to the bar.**

"**Eric how's school going?" Bart said**

"**Good, actually taking a break next week I'm heading to the Hamptons" **

"**Hamptons well why don't you join me and Charles we heading to my Country club next week"**

**Eric certainly didn't want spend an entire week with the Bass men. **

"**That sounds good Mr Bass but I'm going with Serena and her friend Blair as well as Nate Archibald"**

**Chuck looked at Eric confused Nate didn't tell him his heading to the Hamptons next week.**

**Chuck leaned forward towards Eric "Nate? Said he was going"**

"**Well I may have never asked them yet"**

**Chuck smirked he knew Eric just didn't want to go with them to the country club and who could blame him the Bass's aren't exactly Vacation friendly more like sleep with a different girl each night and wake up with a hang over the next morning. Chuck and Bart are defiantly not the father and son type you can sense when there's a bad vibe between them. Bart wants Chuck to head off to college but instead chuck bought a burlesque club called "Victrola" and one of New York's number one hotel's "The Empire Hotel" Bart would be lying if he said he wasn't proud of Charles for buying the Empire but when it comes to other things like drinking and drugs Bart looks down on Chuck no questions asked Bart also wants' chuck to find someone a girl instead of a different one every night he keeps telling chuck his 19 he needs to find someone but Chuck is Defiantly not the dating type or the falling in love.**

"**Talking about Serena good god were is that girl?" Lily said for once sounding like a concerned parent **

**Just then the Elevator bell rang and out came Serena and Blair.**

"**Sorry mom there was traffic" Serena replied looking around she saw Bart and Chuck who hasn't even looked up yet.**

"**Blair! OMG it's him!" Serena whispered to Blair **

"**It's who?"**

"**Chuck Bass" she said as she pointed to him sitting at the end of the table with a glass of scotch in his hand.**

**Blair looked up at him crap she thought she didn't want him to see her after that limo ride home yesterday night she was hoping that was the last time she would ever have to see him.**

"**Serena Blair! Darling's come sit down" Lily said **

**Chuck finally looked up his jaw dropped in shock to see Blair at the same time his heart was pounding out of his chest he wondered if everyone could see the outline of his heart through his suite, Chuck continued to watch her as Lily guided them to their seats Serena took and seat next to Bart, Chuck's heart continued to beat course the only available seat was next to him. Blair looked around for a seat "Blair over here!" Serena shouted pointing to the seat next to her that was also next to Chuck she continued to her seat as both her and Chuck stared at each other with intense eyes.**

**XOXO**

"**Once Blair and everyone was finally seated and all the guest have arrived, Serena and Blair kept whispering in each other's ears Blair trying to avoid Chuck and Serena trying to avoid Eric who was still mad and Serena from earlier on, because Serena didn't tell him she broke up with Dan.  
"So Blair is it? Nice name" he winked at her.  
But Blair wasn't interested she just gave him a glare as she continued to sip her Champagne knowing this was going to be a long night.**

**Chuck continued to make inappropriate innuendos referring to last night which no one seem to pick up but Blair, who kicked him from under the table.**

'**So Charles" lily finally spoke up "you're dad tell me you want to expand the Empire?"  
"Yes we looking to build in Malian, London possibly Miami"  
Chuck said trying to impress Blair.  
"Well that is great! I'm sure you will accomplish that"  
Chuck turned to Blair only to find her slowly eating on her salad  
"Vegetarian Waldorf? Or just not much of an eater?" Chuck smirked  
"Listen Bass, I don't know what the hell you want from me but can we just forget last night ever happened in fact nothing happen last night you just gave me a lift home, so I see no reason for us to interact"  
"Is that so? Admit you felt it" Chuck said as he grabbed her hand from under the table which sent more shiver's not Blair's spin right down to her core.**

**Blair sighed as she got up and pulled her hand away from Chuck's dropping her napkin on the table, she saw that some of the guests were already leaving.**

"**Well um thank you for dinner Lily but I have to get home now my mom is re turning from Paris tomorrow morning" Blair said as she got up to greet Lily and Serena  
"By B" Serena whispered back to her  
"thanks for joining us Blair, and tell your mom I'll come visit her tomorrow when she return" Blair replied **

"**the pleasure is all mine, I will" Blair said as she walked towards the Elevator door she fixed Chuck and finale glare. **

"**Looks like I have to go too" Chuck said getting up from his table fixing his bow tie and greeting Lily, Serena and Eric along with the other guest's. Chuck rushed the Elevator to find Blair only getting in now "Hold it!" Chuck said as he rushed into the Elevator that was about to close.**

**XOXO**

**Okay so I wanted to End this chapter abit disappointing like there's no chuck&Blair kiss so the next chapter that I'm working on is a continuation of what just happen so it will start off of them in the Elevator or out not sure haven't decided yet okay so I'm very young and not a very good writer haha! So if you could please review this is indeed my first story that doesn't really have any relation to chuck Blair's story line anyway until next time xoxo –Ali **


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